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Collision‐activated dissociation studies of alkylamines formed from copper‐induced dealkylation of N ‐alkylporphyrins
Author(s) -
Naylor Stephen,
Gibbs Anthony H.,
Lamb John H.,
De Matteis Francesco
Publication year - 1990
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.1290041013
Subject(s) - chemistry , alkyl , nucleophile , alkylation , dissociation (chemistry) , adduct , medicinal chemistry , fragmentation (computing) , amine gas treating , copper , organic chemistry , catalysis , computer science , operating system
A low‐energy (5–450 eV) collision‐activated dissociation (CAD) study of a series of aliphatic amines revealed that at collision energies above 200 eV, charge‐site‐initiated fragmentation occurs. The resulting fragment ions can be utilized in the characterization of alkyl substituents of di‐ and trisubstituted aliphatic amines. In the presence of Cu 2+ and a suitable nucleophile, such as n‐dodecylamine, N ‐alkyl protoporphyrins dealkylate to afford copper protoporphyrin and an alkyl‐dodecylamine adduct. A CAD study of a number of alkyl‐dodecylamine adducts derived from the copper‐induced dealkylation of synthetic N ‐alkyl protoporphyrins, using charge‐site‐initiated fragment ions, showed that the alkyl group was trapped by the nucleophilic amine present. Subsequently this method was used to identify the alkyl group of a biologically derived N ‐alkyl protoporphyrin.